EP2507330B1 - Procédé de fabrication d'encre au latex en lot unique - Google Patents
Procédé de fabrication d'encre au latex en lot unique Download PDFInfo
- Publication number
- EP2507330B1 EP2507330B1 EP09851941.6A EP09851941A EP2507330B1 EP 2507330 B1 EP2507330 B1 EP 2507330B1 EP 09851941 A EP09851941 A EP 09851941A EP 2507330 B1 EP2507330 B1 EP 2507330B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- latex
- ink
- acid
- pigment
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Not-in-force
Links
- 239000004816 latex Substances 0.000 title claims description 78
- 229920000126 latex Polymers 0.000 title claims description 78
- 238000000034 method Methods 0.000 title claims description 34
- 239000000049 pigment Substances 0.000 claims description 48
- 239000000178 monomer Substances 0.000 claims description 42
- 239000004094 surface-active agent Substances 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 230000001804 emulsifying effect Effects 0.000 claims description 4
- 239000004971 Cross linker Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000006184 cosolvent Substances 0.000 claims description 2
- 230000003247 decreasing effect Effects 0.000 claims description 2
- 239000000976 ink Substances 0.000 description 54
- -1 without limitation Substances 0.000 description 41
- 239000000203 mixture Substances 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 239000003981 vehicle Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 6
- CUTWSDAQYCQTGD-UHFFFAOYSA-N 2-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)C(C)OC(=O)C=C CUTWSDAQYCQTGD-UHFFFAOYSA-N 0.000 description 6
- 229940091181 aconitic acid Drugs 0.000 description 6
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 6
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229940093476 ethylene glycol Drugs 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 3
- STVDIZSDTABYLF-UHFFFAOYSA-N 2-[hydroxy(prop-2-enoyl)amino]acetic acid Chemical compound OC(=O)CN(O)C(=O)C=C STVDIZSDTABYLF-UHFFFAOYSA-N 0.000 description 3
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 3
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- XBACSBFKXGHTIS-UHFFFAOYSA-N 2-methyl-5-sulfopent-2-enoic acid Chemical compound OC(=O)C(C)=CCCS(O)(=O)=O XBACSBFKXGHTIS-UHFFFAOYSA-N 0.000 description 3
- QYHGKNBHPLUAJQ-UHFFFAOYSA-N 2-methylidene-4-sulfobutanoic acid Chemical compound OC(=O)C(=C)CCS(O)(=O)=O QYHGKNBHPLUAJQ-UHFFFAOYSA-N 0.000 description 3
- HIWGDJVTAWTBNH-UHFFFAOYSA-N 2-methylidene-5-sulfopentanoic acid Chemical compound OC(=O)C(=C)CCCS(O)(=O)=O HIWGDJVTAWTBNH-UHFFFAOYSA-N 0.000 description 3
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 3
- UYRCWWINMMLRGJ-UHFFFAOYSA-N 3-ethenoxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOC=C UYRCWWINMMLRGJ-UHFFFAOYSA-N 0.000 description 3
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 3
- RRSZVVDCGQSKIK-UHFFFAOYSA-N 4-(ethenylamino)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC=C RRSZVVDCGQSKIK-UHFFFAOYSA-N 0.000 description 3
- IETVQHUKTKKBFF-UHFFFAOYSA-N 4-vinylphenol sulfate Chemical compound OS(=O)(=O)OC1=CC=C(C=C)C=C1 IETVQHUKTKKBFF-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 3
- QJSFUOBKBXVTMN-UHFFFAOYSA-N C=C.P(O)(O)=O Chemical compound C=C.P(O)(O)=O QJSFUOBKBXVTMN-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid Chemical compound C\C=C(\C)C(O)=O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 3
- 229940018557 citraconic acid Drugs 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 description 3
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical compound OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 description 3
- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 description 3
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 3
- 150000003948 formamides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 3
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 3
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004334 sorbic acid Substances 0.000 description 3
- 235000010199 sorbic acid Nutrition 0.000 description 3
- 229940075582 sorbic acid Drugs 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 238000003917 TEM image Methods 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- 150000003869 acetamides Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960001484 edetic acid Drugs 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
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- 230000000813 microbial effect Effects 0.000 description 2
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- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
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- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- XTJDUBPOTVNQPI-UHFFFAOYSA-N (2-nonylphenyl) 2-methylprop-2-enoate Chemical class CCCCCCCCCC1=CC=CC=C1OC(=O)C(C)=C XTJDUBPOTVNQPI-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- XFOYMWPSASGDSQ-UHFFFAOYSA-N 1-[2-(2-hydroxyethoxy)ethoxy]butan-2-ol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCC(O)COCCOCCO XFOYMWPSASGDSQ-UHFFFAOYSA-N 0.000 description 1
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 1
- YKTLORWZASWBIG-UHFFFAOYSA-N 2-(prop-2-enoylamino)prop-2-enoic acid Chemical compound OC(=O)C(=C)NC(=O)C=C YKTLORWZASWBIG-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
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- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
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- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
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- PSSYEWWHQGPWGA-UHFFFAOYSA-N [2-hydroxy-3-[2-hydroxy-3-(2-hydroxy-3-prop-2-enoyloxypropoxy)propoxy]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)COCC(O)COCC(O)COC(=O)C=C PSSYEWWHQGPWGA-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
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- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 125000000962 organic group Chemical group 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
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- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
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- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
Definitions
- ink-jet printing has become a popular way of recording images on various media surfaces, particularly paper and photo media substrates. Some of these reasons include low printer noise, capability of high-speed recording, and capability of multi-color recording. Additionally, these advantages can be obtained at a relatively low price to consumers.
- ink-jet ink chemistry the majority of commercial ink-jet inks are water-based. Thus, their constituents are generally water-soluble, as in the case with many dyes, or water dispersible, as in the case with pigments.
- ink-jet inks have low viscosity to accommodate high frequency jetting and firing chamber refill processes common to thermal ink-jet architecture.
- liquid vehicle refers to the fluid in which the colorant of the present disclosure can be dispersed or dissolved to form an ink-jet ink.
- Liquid vehicles are well known in the art, and a wide variety of ink vehicles may be used in accordance with embodiments of the present disclosure.
- Such ink vehicles may include a mixture of a variety of different agents, including without limitation, surfactants, organic solvents and co-solvents, buffers, biocides, viscosity modifiers, sequestering agents, stabilizing agents, anti-kogation agents, and water.
- liquid vehicle can carry solid additives such as polymers, latexes, UV curable materials, plasticizers, salts, etc.
- aqueous liquid vehicle or “aqueous vehicle” refers to a liquid vehicle including water as a solvent.
- pigment generally includes pigment colorants, magnetic particles, aluminas, silicas, and/or other ceramics, organo-metallics or other opaque particles, whether or not such particulates impart color.
- pigment colorants generally includes pigment colorants, magnetic particles, aluminas, silicas, and/or other ceramics, organo-metallics or other opaque particles, whether or not such particulates impart color.
- pigment colorants can be used more generally to describe not only pigment colorants, but other pigments such as organometallics, ferrites, ceramics, etc. In one specific embodiment, however, the pigment is a pigment colorant.
- substituted means that a hydrogen atom of a compound or moiety is replaced by another atom such as a carbon chain or a heteroatom, which is part of a group referred to as a substituent.
- substituted include, for example, alkyl, alkoxy, aryl, aryloxy, alkenyl, alkenoxy, alkynyl, alkynoxy, thioalkyl, thioalkenyl, thioalkynyl, and thioaryl.
- heteroatom refers to nitrogen, oxygen, phosphorus, or sulfur.
- halo and halogen refer to a fluoro, chloro, bromo, or iodo substituent.
- cyclic refers to having an alicyclic or aromatic ring structure, which may or may not be substituted, and may or may not include one or more heteroatoms. Cyclic structures include monocyclic structures, bicyclic structures, and polycyclic structures. The term “alicyclic” is used to refer to an aliphatic cyclic moiety, as opposed to an aromatic cyclic moiety.
- alkyl refers to a branched, unbranched, or cyclic saturated hydrocarbon group, which typically, although not necessarily, contains from 1 to about 50 carbon atoms, or 1 to about 40 carbon atoms, or 1 to about 30 carbon atoms, for example.
- Alkyls include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, octyl, and decyl, for example, as well as cycloalkyl groups such as cyclopentyl, and cyclohexyl, for example.
- lower alkyl refers to an alkyl group having from 1 to 6 carbon atoms.
- higher alkyl refers to an alkyl group having more than 6 carbon atoms, for example, 7 to about 50 carbon atoms, or 7 to about 40 carbon atoms, or 7 to about 30 carbon atoms or more.
- substituted alkyl refers to an alkyl substituted with one or more substituent groups.
- heteroalkyl refers to an alkyl in which at least one carbon atom is replaced with a heteroatom. If not otherwise indicated, the term “alkyl” includes unsubstituted alkyl, substituted alkyl, lower alkyl, and heteroalkyl.
- aryl refers to a group containing a single aromatic ring or multiple aromatic rings that are fused together, directly linked, or indirectly linked (such that the different aromatic rings are bound to a common group such as a methylene or ethylene moiety).
- Aryl groups described herein may contain, but are not limited to, from 5 to about 50 carbon atoms, or 5 to about 40 carbon atoms, or 5 to 30 carbon atoms or more.
- Aryl groups include, for example, phenyl, naphthyl, anthryl, phenanthryl, biphenyl, diphenylether, diphenylamine, and benzophenone.
- substituted aryl refers to an aryl group comprising one or more substituent groups.
- heteroaryl refers to an aryl group in which at least one carbon atom is replaced with a heteroatom. If not otherwise indicated, the term “aryl” includes unsubstituted aryl, substituted aryl, and heteroaryl.
- the term "about” is used to provide flexibility to a numerical range endpoint by providing that a given value may be "a little above” or “a little below” the endpoint.
- the degree of flexibility of this term can be dictated by the particular variable and would be within the knowledge of those skilled in the art to determine based on experience and the associated description herein.
- the present disclosure is drawn to compositions and methods, wherein at least one reaction condition of the polymerization is modified to provide a single batch latex ink-jet ink.
- the composition and method provides specific size parameters for the resulting latex particles and encapsulated pigments. It is noted that when discussing the present methods and associated compositions, each of these discussions can be considered applicable to each of these embodiments, whether or not they are explicitly discussed in the context of that embodiment. Thus, for example, in discussing a monomer for use in a method of manufacturing a single batch latex ink-jet ink, such a monomer can also be used for an ink-jet ink composition, and vice versa.
- a method of manufacturing a single batch latex ink-jet ink can comprise emulsifying a pigment and a monomer in a solvent and polymerizing the monomer with a reaction condition sufficient to encapsulate the pigment and sufficient to form individual latex particulates thereby forming a single batch latex ink-jet ink. Additionally, the method can provide a single batch latex ink-jet ink that contains less than 0.5 wt% of latex particulates having a diameter of 50 nm or less, that contains 1 wt% to 10 wt% of latex particulates having a diameter of 100 nm to 250 nm and that contains 3 wt% to 5 wt% of encapsulated pigment. Additionally, the present disclosure provides ink-jet inks manufactured by any of the methods described herein.
- WO 2005/105931 discloses a process for the preparation of polymer-encapsulated pigments and their use as colourants in the printing sector and in ink-jet inks.
- the present method can be carried out to form encapsulated pigments and latexes, which when optionally formulated with other vehicle components, can be directly ink-jetted; i.e., a single batch latex ink-jet ink.
- a few reaction conditions can be modified to provide a single batch latex ink-jet ink.
- reaction conditions that can influence encapsulation as well as latex particulate formation include modifying the amount of dispersant present, varying the viscosity, modifying the amount of surfactant, and/or varying the initiator loading for polymerization.
- the reaction condition sufficient to encapsulate the pigment and sufficient to form individual latex particles having the latex particulate size profiles discussed herein is by decreasing an initiator loading for polymerization by adding a first amount of the initiator to initiate the polymerization and adding a second amount of initiator during polymerization such that the second amount is added over a period of at least 1 hour, and wherein the second amount constitutes at least 30% of total initiator added.
- the second amount can constitute at least 40% of total initiator added.
- the second amount can be added over at least a 3 hour period.
- reaction condition can relate to viscosity of the emulsion, and in some embodiments, can range from about 40 cP to about 70 cP as compared to a comparative ink that has a more traditional emulsion viscosity of about 25 cP. That being said, it is understood that such a viscosity does not necessarily provide a size profile that can be ink-jetted for every latex. Rather, the present methods can be tailored for any specific combination of latex particles and encapsulated pigments.
- the use of a comparative ink provides an objective determination of the necessary reaction condition; i.e., the reaction condition can be those listed above that can change the size profiles of the latex and encapsulated pigment of a comparative ink into the size profiles of the single batch latex ink-jet ink such that the single batch latex ink-jet ink is ink-jettable.
- the reaction condition can be those listed above that can change the size profiles of the latex and encapsulated pigment of a comparative ink into the size profiles of the single batch latex ink-jet ink such that the single batch latex ink-jet ink is ink-jettable.
- the single batch latex ink-jet ink can contain less than 0.1 wt% of latex particulates having a diameter of 50 nm or less and contains 3 wt% to 6 wt% of latex particulates having a diameter of 100 nm to 250 nm. In another embodiment, the latex particulates can have less than 5 wt% of latex particles having a diameter of greater than 500 nm.
- the ratio of weight percents of polymer to pigment can be at least 3:1. In one embodiment, the ratio of weight percents of polymer to pigment can be at least 5:1. Additionally, the ratio of the size of the encapsulated pigment to the size of the latex particulates can be 3:1 to 1:3. In one embodiment, the ratio can be about 2:1.
- the present methods can include multiple dispersing and emulsifying steps.
- dispersing the pigment and monomer can include adding a dispersant.
- forming the emulsion can include adding water and a surfactant.
- forming the emulsion can be by microfluidization.
- the microfluidization can have a liquid shear pressure of 1,000 to 30,000 psi.
- forming the emulsion can be by sonication.
- the single batch latex ink-jet ink can be stored as ready to use.
- the single batch latex ink-jet ink can be filtered through a 10 ⁇ m screen mesh before use or before storage.
- the single batch latex ink-jet ink can be filtered through a 1 ⁇ m screen mesh before use or before storage.
- the pH of the single batch latex ink-jet ink can be about 8 to about 9.
- the latex particulates described herein are generally polymerized from latex monomers as known in the art, or in the case of encapsulated pigments, include polymerized latex monomers.
- the monomer can include a linear aliphatic, branched aliphatic, or cyclic aliphatic acrylate.
- the encapsulated pigment and the latex particulate can include at least one hydrophilic monomer and one hydrophobic monomer.
- the linear aliphatic acrylate, branched aliphatic acrylate, or cyclic aliphatic acrylate can include, but is not limited to, ethyl, propyl, isobutyl, butyl, tertarylbutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, lauryl, cyclohexyl acrylates, and t butylcyclohexyl. Blends of these monomers with heteroatom containing functional monomers can also be used to enhance and fine tune a desire latex property.
- These monomers can include, but are not limited to, 2-hydroxylethyl, 2-hydroxylpropyl, 2-hydroxylbutyl, dimethylaminoethyl, glycidyl, butanediol, 2-carboxylethyl, 2-ethoxyethyl, di(ethylene glycol) methyl ether, ethylene glycol methyl ether, ethylene glycol phenyl ether, 2-(4-benzoyl-3-hydroxyphenoxy)ethyl, 2-(dialkylamino)ethyl, 2-(dialkylamino)propyl, 2-[[(butylamino)carbonyl]-oxy]ethyl, 2-hydroxyl-3-phenoxypropyl, 3,5,5-trimethylhexyl, 3-(trimethyloxysilyl)propyl, 3-sulfopropyl, di(ethylene glycol)-2-ethylhexyl ether, dipentaerythritol penta-/hexa,
- the hydrophobic monomer can be present in the polymer from up to 98 wt%, e.g., in one embodiment, from 50 wt% to 98 wt%.
- Hydrophobic monomers that can be polymerized to form the latex particulate and the encapsulated pigment include, without limitation, styrene, p-methyl styrene, methyl methacrylate, hexyl acrylate, hexyl methacrylate, butyl acrylate, butyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, octadecyl acrylate, octadecyl methacrylate, stearyl methacrylate, vinylbenzyl chloride, isobornyl acrylate, tetrahydrofurfuryl acrylate, 2-phenoxyethyl methacrylate, eth
- the hydrophilic monomer can be present in the polymer from up to 10 wt%, e.g., in one embodiment, from 0.5 wt% to 10 wt%. In another embodiment, the hydrophilic monomer can be present from 3 wt% to 7 wt%.
- Suitable hydrophilic monomers include those containing an ionizable functional group or are otherwise capable of forming an ionic charge after polymerization as well as those that are capable of hydrogen bonding with water or otherwise capable of being solvated in water.
- the hydrophilic monomers can be anionic hydrophilic monomers, nonionic hydrophilic monomers, and cationic hydrophilic monomers.
- the hydrophilic monomer can be an acidic monomer.
- the acidic monomer can be selected from the group consisting of acrylic acid, methacrylic acid, ethacrylic acid, dimethylacrylic acid, maleic anhydride, succinic anhydride, vinylsulfonate, cyanoacrylic acid, methylenemalonic acid, vinylacetic acid, allylacetic acid, ethylidineacetic acid, propylidineacetic acid, crotonoic acid, fumaric acid, itaconic acid, sorbic acid, angelic acid, cinnamic acid, styrylacrylic acid, citraconic acid, glutaconic acid, aconitic acid, phenylacrylic acid, acryloxypropionic acid, aconitic acid, phenylacrylic acid, acryloxypropionic acid, vinylbenzoic acid, N-vinylsuccinamidic acid, mesaconic acid, methacroylalanine,
- Acidic monomers can be present in the polymer from up about 0.1 wt% to about 30 wt.
- Acidic monomers that can be used in the polymer include, without limitation, acrylic acid, methacrylic acid, ethacrylic acid, dimethylacrylic acid, maleic anhydride, maleic acid, vinylsulfonate, cyanoacrylic acid, vinylacetic acid, allylacetic acid, ethylidineacetic acid, propylidineacetic acid, crotonoic acid, fumaric acid, itaconic acid, sorbic acid, angelic acid, cinnamic acid, styrylacrylic acid, citraconic acid, glutaconic acid, aconitic acid, phenylacrylic acid, acryloxypropionic acid, aconitic acid, phenylacrylic acid, acryloxypropionic acid, vinylbenzoic acid, N-vinylsuccinamidic acid, mesaconic acid, methacroylalan
- the polymerization can include adding a cross-linker.
- the crosslinker can be selected from the group consisting of divinylbenzene; ethyleneglycol dimethacrylate; 1,3-butanediol diacrylate; 1,4-butanediol diacrylate; 1,6-hexanediol diacrylate; ethylene glycol diacrylate; glycerol 1,3-diglycerolate diacrylate; pentaerythritol diacrylate monostearate; 1,6-hexanediol ethoxylate diacrylate; 1,6-hexanediol propoxylate diacrylate; bisphenol A ethoxylate diacrylate; bisphenol A propoxylate diacrylate; di(ethylene glycol) diacrylate; poly(ethylene glycol) diacrylate; poly(propylene glycol) diacrylate; tetra(ethylene glycol) diacrylate; and mixtures thereof.
- the polymerization will include an initiator.
- the monomer mix may also contain oil-soluble initiator such as azobisisobutyronitrile, azobis(cyclohexanecarbonitrile), benzoyl peroxide, and mixtures thereof.
- the latex particulates and encapsulated pigments can have a Tg ranging from about -40°C to about 125°C. In one embodiment, the Tg can range from about 15°C to about 45°C. As discussed above, the present ranges include sub-ranges.
- the latex particulates and encapsulated pigments can have a Tg from about 0°C to about 75°C, about 0°C to about 45°C, about 15°C to about 75°C, about 20°C to about 40°C, etc.
- the present methods and compositions can be furthered modified to include known ink-jet ink materials and additives.
- the single batch latex ink-jet ink can include an organic co-solvent.
- Classes of co-solvents that can be used can include organic co-solvents including aliphatic alcohols, aromatic alcohols, diols, glycol ethers, polyglycol ethers, caprolactams, formamides, acetamides, and long chain alcohols.
- Examples of such compounds include primary aliphatic alcohols, secondary aliphatic alcohols, 1,2-alcohols, 1,3-alcohols, 1,5-alcohols, ethylene glycol alkyl ethers, propylene glycol alkyl ethers, higher homologs (C 6 -C 12 ) of polyethylene glycol alkyl ethers, N-alkyl caprolactams, unsubstituted caprolactams, both substituted and unsubstituted formamides, both substituted and unsubstituted acetamides, and the like.
- Specific examples of solvents that can be used include trimethylolpropane, 2-pyrrolidinone, and 1,5-pentanediol.
- the latex particulates and encapsulated pigments described herein can be further stabilized by addition of surfactants.
- the latex particulates and encapsulated pigments can further comprise the addition of a reactive surfactant during the polymerization process.
- the reactive surfactant contains hydrophobic moieties that can be covalently bound to the surface of the polymeric particles.
- such a reactive surfactant can be incorporated during the polymerization via appropriate organic groups, e.g., a vinyl group, such that the surface of the latex particulates and encapsulated pigments contain the reactive surfactant.
- the reactive surfactant can contain hydrophilic groups that allow the latex particulates and encapsulated pigments to be better dispersed and/or stabilized in an aqueous medium.
- the hydrophilic groups can be anionic, cationic, nonionic, or zwitterionic.
- suitable anionic groups include sulfonate, phosphonate, and carboxylate groups
- suitable cationic groups include amine groups
- suitable nonionic groups include polyethelyene oxide, imidazole and amido groups.
- the reactive surfactants can be functionalized ethylene glycol acrylates, including the SIPOMER® series of surfactants from Rhodia.
- reactive surfactants include HITENOLTM (polyoxyethylene alkylphenyl ether ammonium sulfate) and NOIGENTM (polyoxyethylene alkylphenyl ether) reactive surfactants commercially available from Dai-lchi Kogyo Seiyaku Co., Ltd. of Japan; TREM® (sulfosuccinates) commercially available from Henkel; and the MAXEMUL® (anionic phosphate ester) reactive surfactants commercially available from Uniqema of the Netherlands. Suitable grades of some of the materials listed above may include HITENOL BC-20, NOIZEN RN-30, TREM LT-40, and MAXEMUL 6106 and 6112.
- surfactants can also be used as are known by those skilled in the art of ink formulation and may be alkyl polyethylene oxides, alkyl phenyl polyethylene oxides, polyethylene oxide block copolymers, acetylenic polyethylene oxides, polyethylene oxide (di)esters, polyethylene oxide amines, protonated polyethylene oxide amines, protonated polyethylene oxide amides, dimethicone copolyols, substituted amine oxides, and the like.
- the amount of surfactant added to the formulation, if included, may range from 0.01 wt% to 10.0 wt%.
- the surfactant that is described as being usable in the ink need not be the same as the surfactant that is used during emulsifying or as described as being adhered to the surface of the latex particulates and encapsulated pigments as previously described, though many of the same surfactants can be used for either purpose.
- additives may be employed to optimize the properties of the ink composition for specific applications.
- these additives are those added to inhibit the growth of harmful microorganisms.
- These additives may be biocides, fungicides, and other microbial agents, which are routinely used in ink formulations.
- suitable microbial agents include, but are not limited to, NUOSEPT® (Nudex, Inc.), UCARCIDETM (Union carbide Corp.), VANCIDE® (R.T. Vanderbilt Co.), PROXEL® (ICI America), and combinations thereof.
- Sequestering agents such as EDTA (ethylene diamine tetra acetic acid) may be included to eliminate the deleterious effects of heavy metal impurities, and buffer solutions may be used to control the pH of the ink. From 0 wt% to 2.0 wt%, for example, can be used. Viscosity modifiers and buffers may also be present, as well as other additives known to those skilled in the art to modify properties of the ink as desired. Such additives can be present at from 0 wt% to 20.0 wt%.
- EDTA ethylene diamine tetra acetic acid
- the ink-jet ink compositions of the present disclosure may also be suitable for use on many types of substrates of recording media, including but not limited to vinyl media, cellulose-based paper media, various cloth materials, polymeric materials (non-limitative examples of which include polyester white film or polyester transparent film), photopaper (non-limiting examples of which include polyethylene or polypropylene extruded on one or both sides of paper), metals, and/or mixtures or composites thereof.
- a non-limiting example of a suitable metal material is a metal in foil form made from, for example, at least one of aluminum, silver, tin, copper, alloys thereof, and/or mixtures thereof.
- Example 1 Single batch Latex Ink-Jet Ink
- a single batch latex ink-jet ink was made by mixing 10 mL of monomers (styrene, hexylmethacrylate, acrylic acid (40:55:5)) with 0.25 g of AIBN and 5 g of BASF D7086 cyan pigment by mechanical stirring.
- the resulting paste was subsequently dispersed into a degassed deionized aqueous solution (200 mL) containing 1.5 g sodium dodecyl sulfate also by mechanical mixing until the homogenous suspension was obtained.
- the resulting suspension further underwent microfluidization (Microfluidics M110-Y) at a pressure of 10,000 psi at a rate of 200 mL/min for 15 minutes.
- the stabilized emulsion was collected into a reaction vessel equipped with a magnetic stir bar and a condenser, and then heated to 80 °C under a stream of argon.
- an aqueous solution of potassium persulfate (0.2 g in 15 mL water) was added to the reaction dropwise via an addition funnel over the course of 3 hours.
- the polymerization was allowed to proceed for an additional 3 hours until all monomers were consumed.
- the newly formed latex ink was allowed to cool to room temperature, and then saturated potassium hydroxide was added to this solution at room temperature with stirring until the pH reached 8.5.
- the latex ink was then screened through a 20 micron aluminum mesh into a storage bottle until use.
- Example 1 The single batch ink-jet ink having the components of Example 1 was prepared without the continuous addition of potassium persulfate, resulting in a comparative ink having higher percentage of smaller latex particles.
- the ink of Example 1 provided larger latex particles than the comparative ink of Example 2, and further, the ink of Example 1 was ink-jettable without modification. Specifically, the ink of Example 1 contained a significant majority of latex particulates having a diameter of 100 nm to 250 nm, as shown in FIG. 1 , while the comparative ink was not ink-jettable due to the large presence of latex particulates having a diameter of 50 nm or less, as shown in FIG. 2 .
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Claims (13)
- Procédé de fabrication d'une encre pour jet d'encre à base de latex en lot unique, comprenant consistant à : émulsionner un pigment et un monomère dans un solvant pour former une émulsion ; et
polymériser le monomère dans une condition de réaction suffisante pour encapsuler le pigment et suffisante pour former des particules de latex individuelles, la condition de réaction suffisante pour encapsuler le pigment et suffisante pour former des particules de latex individuelles étant la diminution d'une charge d'amorceur pour la polymérisation par addition d'une première quantité de l'amorceur pour amorcer la polymérisation et l'ajout d'une seconde quantité d'amorceur pendant la polymérisation de sorte que la seconde quantité est ajoutée sur une période d'au moins 1 heure, et la seconde quantité représentant au moins 30% de l'amorceur total ajouté, de façon à former une encre pour jet d'encre à base de latex en lot unique qui comprend moins de 0,5% en poids de particules de latex d'un diamètre de 50 nm ou moins, de 1% en poids à 10% en poids de particules de latex d'un diamètre de 100 nm à 250 nm, et de 3% en poids à 5% en poids du pigment encapsulé. - Procédé selon la revendication 1, dans lequel l'encre pour jet d'encre à base de latex en lot unique contient moins de 0,1% en poids de particules de latex d'un diamètre de 50 nm ou moins, et contient de 3% en poids à 6% en poids de particules de latex d'un diamètre de 100 nm à 250 nm.
- Procédé selon l'une quelconque des revendications 1 à 2, dans lequel le rapport du polymère au pigment est d'au moins 3:1 en poids.
- Procédé selon l'une quelconque des revendications 1 à 3, dans lequel les particules de latex ont moins de 5% en poids de particules de latex d'un diamètre supérieur à 500 nm.
- Procédé selon l'une quelconque des revendications 1 à 4, dans lequel l'encre pour jet d'encre à base de latex à lot unique est filtrée à travers un maillage de tamis de 10 µm avant utilisation.
- Procédé selon l'une quelconque des revendications 1 à 5, comprenant en outre l'étape consistant à former l'émulsion par microfluidisation ayant une pression de cisaillement de liquide de 1000 à 30000.
- Procédé selon l'une quelconque des revendications 1 à 6, comprenant en outre l'étape consistant à disperser le pigment et le monomère par addition d'un dispersant.
- Procédé selon l'une quelconque des revendications 1 à 7, dans lequel l'émulsion comprend de l'eau et un tensioactif.
- Procédé selon l'une quelconque des revendications 1 à 8, dans lequel le monomère comprend un groupe acrylate aliphatique linéaire, aliphatique ramifié, ou aliphatique cyclique.
- Procédé selon l'une quelconque des revendications 1 à 9, dans lequel le pigment encapsulé et les particules de latex comprennent au moins un monomère hydrophile et d'un monomère hydrophobe.
- Procédé selon l'une quelconque des revendications 1 à 10, dans lequel l'étape de polymérisation comprend l'addition d'un agent de réticulation.
- Procédé selon l'une quelconque des revendications 1 à 11, dans lequel l'encre pour jet d'encre à base de latex à lot unique comprend un co-solvant organique.
- Procédé selon l'une quelconque des revendications 1 à 12, dans lequel la taille du pigment encapsulé à la taille des particules de latex est de 2:1 à 1:2.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2009/066851 WO2011068521A1 (fr) | 2009-12-04 | 2009-12-04 | Compositions d'encre au latex en lot unique et procédés |
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| EP2507330A1 EP2507330A1 (fr) | 2012-10-10 |
| EP2507330A4 EP2507330A4 (fr) | 2013-05-15 |
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| EP (1) | EP2507330B1 (fr) |
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| WO2011014195A1 (fr) * | 2009-07-31 | 2011-02-03 | Hewlett-Packard Development Company, L.P. | Encapsulation polymère de particules |
| WO2013178261A1 (fr) | 2012-05-30 | 2013-12-05 | Hewlett-Packard Development Company, L.P. | Distribution d'un écoulement d'air à un support d'impression |
| JP7653070B2 (ja) * | 2020-09-24 | 2025-03-28 | セイコーエプソン株式会社 | 分散液、インクジェット記録用インク組成物、及び分散樹脂 |
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| US6877850B2 (en) * | 2001-04-24 | 2005-04-12 | Seiko Epson Corporation | Ink jet recording method, ink set, and recorded matter using them |
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| JP2003034770A (ja) * | 2001-05-17 | 2003-02-07 | Fuji Photo Film Co Ltd | 水系着色微粒子分散物、その製造方法、およびインクジェット記録用インク |
| JP2002363460A (ja) | 2001-06-06 | 2002-12-18 | Konica Corp | 着色微粒子含有水性インク及び画像形成方法 |
| US6848777B2 (en) * | 2002-09-27 | 2005-02-01 | Eastman Kodak Company | Aqueous inkjet ink and receiver combination |
| US6764173B2 (en) | 2002-09-27 | 2004-07-20 | Eastman Kodak Company | Inkjet printing method |
| US7119133B2 (en) | 2003-02-06 | 2006-10-10 | Hewlett-Packard Development Company, L.P. | Latex-encapsulated particulates for ink-jet applications |
| DE10348464A1 (de) * | 2003-10-14 | 2005-05-19 | Basf Ag | Formulierungen und ihre Verwendungen bei der Kolorierung von Substraten |
| EP1756237B1 (fr) | 2004-03-18 | 2017-05-03 | Hewlett-Packard Development Company, L.P. | Particules encapsulees dans du latex pour applications de jet d'encre |
| DE102004020726A1 (de) * | 2004-04-28 | 2005-11-24 | Clariant Gmbh | Verfahren zur Herstellung polymerverkapselter Pigmente |
| MY146025A (en) * | 2004-10-04 | 2012-06-15 | Univ Sydney | Polymerisation process and polymer product |
| JP5105757B2 (ja) | 2006-03-15 | 2012-12-26 | 富士フイルム株式会社 | インクジェット記録用インクセット及びインクジェット記録方法 |
| US7608646B1 (en) | 2006-04-28 | 2009-10-27 | Hewlett-Packard Development Company, L.P. | Polymer-encapsulated pigment with bridging layer |
| US7544418B2 (en) | 2006-07-31 | 2009-06-09 | Hewlett-Packard Development Company, L.P. | Polymer-encapsulated pigments and associated methods |
| US20080250971A1 (en) | 2007-04-16 | 2008-10-16 | Sivapackia Ganapathiappan | Polymer-encapsulated pigment with passivation layer |
| US8318833B2 (en) * | 2007-04-26 | 2012-11-27 | Hewlett-Packard Development Company, L.P. | Polymer-encapsulated pigment with amphiphilic passivation layer |
| US8383701B2 (en) | 2007-05-04 | 2013-02-26 | Hewlett-Packard Development Company, L.P. | Polymer encapsulated pigment dispersion with high solids content |
| WO2009064278A1 (fr) | 2007-11-15 | 2009-05-22 | Hewlett-Packard Development Company, L.P. | Pigments encapsulés dans des polymères |
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- 2009-12-04 CN CN200980162727.7A patent/CN102712823B/zh not_active Expired - Fee Related
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- 2009-12-04 EP EP09851941.6A patent/EP2507330B1/fr not_active Not-in-force
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6877850B2 (en) * | 2001-04-24 | 2005-04-12 | Seiko Epson Corporation | Ink jet recording method, ink set, and recorded matter using them |
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| US20120232215A1 (en) | 2012-09-13 |
| EP2507330A1 (fr) | 2012-10-10 |
| EP2507330A4 (fr) | 2013-05-15 |
| CN102712823A (zh) | 2012-10-03 |
| CN102712823B (zh) | 2014-10-01 |
| US8772369B2 (en) | 2014-07-08 |
| WO2011068521A1 (fr) | 2011-06-09 |
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